He never does. The Sage of the Six Paths is a legendary historical figure who defeated the 10-tailed beast and took it inside himself, then later split it into 9 seperate tailed beasts. His main power was the Rinnegan, a powerful ocular jutsu.
Naruto is able to go into a 'sage mode' through collecting natural energy and merging it with his own chakra. This is not in any way related to the Sage of the Six Paths.
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Naruto Shippuden. Episode 60 or 61 :)
Um the naruto shippuden episodes haven't caught up to that part yet...their still on the pein saga (according to Naruto.com) Buuuuutttt, in the manga its chapter 484 page 16-17 to be excat :) Sasuke...what happen to you....You can read that chapter and all the other ones on onemanga.com
The Targeted Shukaku saga begins with episode 216 and ends with episode 220.
Naruto Shippuuden does not have "Seasons". It has Sagas (like all Anime series') The Saga in which Naruto defeats Pain is called the "Pain Invasion Arc".
In the Majin Buu Saga after Buu was resurrected. When Vegeta was in the heavens after he died, he saw Goku go SS3 and accused Goku of mocking him with that transformation. In case you were looking for the episode number it was episode 245